Cycloalkyl carboxylic acid amides, their production and their use as fungicides in agriculture

Abstract

The present invention relates to cycloalkylcarboxamides of formula I where: A is optionally substituted C 3 -C 6 -cycloalkyl; Alk is straight-chain or branched C 1 -C 6 -alkylene; R 1 is optionally substituted C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl; R 2 , R 3 is hydrogen, or is optionally halogenated C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl; W is an optionally substituted fused bicyclic ring system having in each case six ring atoms, where one or two carbon ring atoms may be replaced by nitrogen atoms; and their agriculturally useful salts. Furthermore, the invention relates to fungicidal compositions comprising a compound of formula I as crop protection agent.

We claim:  
     
       1. A cycloalkylcarboxamide of the formula Ia                    
       where: 
       Alk is straight-chain or branched C 1 -C 6 -alkylene;  
       R 1  is C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, where these radicals may be partially or fully halogenated and/or may carry one or two of the following groups: C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl and phenyl, where the phenyl may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl or heterocyclyl;  
       R 2 , R 3  are hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, where these radicals may be partially or fully halogenated;  
       W is a fused bicyclic ring system having in each case six ring atoms, where one or two carbon ring atoms may be replaced by nitrogen atoms, and where these ring systems may carry one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl and C 1 -C 4 -alkoxycarbonyl;  
       R 4  is hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, where these radicals may be partially or fully halogenated and/or may carry one or two of the following groups: C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxycarbonylamino;  
       R 5  is hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, where these radicals may be partially or fully halogenated and/or may carry one or two of the following groups: C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxycarbonylamino;  
       R 6  is hydrogen, halogen or C 1 -C 6 -alkyl;  
       R 7  is hydrogen, halogen or C 1 -C 6 -alkyl;  
       R 8  is hydrogen, halogen or C 1 -C 6 -alkyl,  
       and their agriculturally useful salts. 
     
     
       2. A cycloalkylcarboxamide of the formula Ia as claimed in  claim 1 , where the cyclopropyl ring may carry one to five substituents R 4 -R 8  selected from the group of the radicals consisting of halogen, cyano and C 1 -C 3 -alkyl. 
     
     
       3. A cycloalkylcarboxamide as claimed in  claim 1 , where R 4  is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio. 
     
     
       4. A cycloalkylcarboxamide as claimed in in  claim 1 , where R 5  is hydrogen or C 1 -C 6 -alkyl. 
     
     
       5. A cycloalkylcarboxamide as claimed in  claim 1 , where R 6  is hydrogen or C 1 -C 6 -alkyl. 
     
     
       6. A cycloalkylcarboxamide as claimed in  claim 1 , where R 7  is hydrogen, chlorine or C 1 -C 6 -alkyl. 
     
     
       7. A cycloalkylcarboxamide as claimed in  claim 1 , where R 8  is hydrogen, chlorine or C 1 -C 6 -alkyl. 
     
     
       8. A cycloalkylcarboxamide as claimed in  claim 1 , where R 1  is C 1 -C 6 -alkyl and R 2  is hydrogen or C 1 -C 6 -alkyl. 
     
     
       9. A cycloalkylcarboxamide as claimed in  claim 1 , where Alk is a methylene group. 
     
     
       10. A composition comprising a fungicidally effective amount of at least one cycloalkylcarboxamide of the formula I as claimed in  claim 1  and, if appropriate, an inert liquid and/or solid carrier and, if appropriate, at least one surfactant. 
     
     
       11. A method for controlling harmful fungi, which comprises treating the harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them with an effective amount of a cycloalkylalkanecarboxamide of the formula I as claimed in  claim 1 .